Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases

ABSTRACT

An agricultural or horticultural chemical according to the present invention is an agricultural or horticultural chemical containing a plurality of active ingredients, the agricultural or horticultural chemical comprises, as one of the active ingredients, an azole derivative represented by general formula (I), and can be used as a plant disease controlling agent that can reduce the content of an active ingredient: 
     
       
         
         
             
             
         
       
     
     wherein, R 1  represents an alkyl group having from 1 to 6 carbons, R 2  represents a hydrogen atom, an alkyl group having from 1 to 3 carbons, an alkenyl group or an alkynyl group having from 2 to 3 carbons, A represents a nitrogen atom or a methine group, Y 1  represents a halogen atom, and n represents either 0 or 1.

TECHNICAL FIELD

The present invention relates to an agricultural or horticulturalchemical, a method of controlling plant diseases, and a product forcontrolling plant diseases. In particular, the present invention relatesto an agricultural or horticultural chemical containing at least onetype of azole-based compound as an active ingredient, a method ofcontrolling plant diseases using the same, and a product for controllingplant diseases containing the azole-based compound.

BACKGROUND ART

Certain types of 2-substituted-5-benzyl-1-azolyl methyl cyclopentanolderivatives have been known to exhibit fungicidal activity (e.g. referto Patent Documents 1 to 3).

CITATION LIST Patent Literature

Patent Document 1: Japanese Unexamined Patent Application PublicationNo. H01-93574A (published on Apr. 12, 1989)

Patent Document 2: Japanese Unexamined Patent Application PublicationNo. H01-186871A (published on Jul. 26, 1989)

Patent Document 3: WO/2012/169516 (published on Dec. 13, 2012)

SUMMARY OF INVENTION Technical Problem

To-date, agricultural and horticultural chemicals having low toxicitytoward human and animals and excellent safety in handling, andexhibiting a high controlling effect against a wide variety of plantdiseases have been demanded.

Disease control by agricultural and horticultural chemicals has alsoraised problems such as the effect on non-target organisms, the effecton the environment, and the emergence of chemical-resistant fungi. Forthat reason, to reduce toxicity in non-target organisms, to reduceenvironmental load, and to suppress the emergence of chemical-resistantfungi, an agricultural or horticultural chemical that can exhibit astrong controlling effect with a reduced dispersion quantity has beendesired.

The present invention has been completed in the light of the aboveproblems. An object of the present invention is to provide anagricultural or horticultural chemical exhibiting an excellentcontrolling effect and requiring a smaller amount of dispersion toobtain the same degree of effect as that of conventional chemicals.

Solution to Problem

The agricultural or horticultural chemical of the present invention isan agricultural or horticultural chemical containing a plurality ofactive ingredients, the agricultural or horticultural chemicalcomprising: as one of the active ingredients, an azole derivativerepresented by general formula (I) below; and, as another one of theactive ingredients, a compound having a cell membrane ergosterolbiosynthesis inhibitory capacity.

In formula (I), R¹ represents an alkyl group having from 1 to 6 carbons;R² represents a hydrogen atom, an alkyl group having from 1 to 3carbons, an alkenyl group having from 2 to 3 carbons, or an alkynylgroup having from 2 to 3 carbons;

A represents a nitrogen atom or a methine group; Y¹ represents a halogenatom; and n represents either 0 or 1.

The product for controlling plant diseases of the present invention hasa constitution separately comprising, as a combination preparation bywhich a plurality of active ingredients are mixed for use: an azolederivative represented by general formula (I) above; and a compoundhaving a cell membrane ergosterol biosynthesis inhibitory capacity.

The method of controlling plant diseases of the present inventioncomprises a step of performing foliage treatment or non-foliagetreatment using the agricultural or horticultural chemical describedabove.

Advantageous Effects of Invention

Since the agricultural or horticultural chemical of the presentinvention contains a plurality of compounds as active ingredients, theagricultural or horticultural chemical can exhibit a synergistic effectand can demonstrate a strong controlling effect.

DESCRIPTION OF EMBODIMENTS

An embodiment of the agricultural or horticultural chemical, the productfor controlling plant diseases, and the method of controlling plantdiseases of the present invention will be described.

Agricultural or Horticultural Chemical

The agricultural or horticultural chemical of the present invention is amixed formulation and contains a plurality of active ingredients. One ofthe active ingredients is an azole derivative represented by generalformula (I) below. That is, the agricultural or horticultural chemicalof the present invention contains at least one other compound as theactive ingredient(s) in addition to the azole derivative represented bythe general formula (I). The agricultural or horticultural chemical ofthe present invention contains, as one of the active ingredients, acompound having a cell membrane ergosterol biosynthesis inhibitorycapacity in addition to an azole derivative represented by generalformula (I).

(1) Active Ingredients (1-1) Azole Derivative

The agricultural or horticultural chemical according to the presentinvention contains, as one of the active ingredients, an azolederivative represented by general formula (I) below (hereinafter,referred to as azole derivative (I)).

In general formula (I), R¹ represents an alkyl group having from 1 to 6carbons. Examples of the alkyl group having from 1 to 6 carbons includea methyl group, ethyl group, (1-methyl)ethyl group, n-propyl group,1-methylpropyl group, 2-methylpropyl group, n-butyl group, 1-methylbutylgroup, 2-methylbutyl group, 1-ethylpropyl group, 1,1-dimethylethylgroup, n-pentyl group, n-hexyl group, and the like. Among these, analkyl group having from 1 to 4 carbons is preferable as R¹, a methylgroup and an ethyl group are more preferable, and a methyl group isstill more preferable.

In general formula (I), R² represents a hydrogen atom, an alkyl grouphaving from 1 to 3 carbons, an alkenyl group having from 2 to 3 carbonsor an alkynyl group having from 2 to 3 carbons. Examples of the alkylgroup having from 1 to 3 carbons include a methyl group, ethyl group,(1-methyl)ethyl group, and n-propyl group. Examples of the alkynyl grouphaving from 2 to 3 carbons include a vinyl group and a 2-propenyl group.An example of the alkynyl group having from 2 to 3 carbons is a2-propynyl group. Of these, a hydrogen atom, a methyl group, an ethylgroup, and an n-propyl group are preferable as R², and a methyl group ismore preferable.

In general formula (I), Y¹ represents a halogen atom. More specifically,examples of the halogen atom include a chlorine atom, a fluorine atom, abromine atom, and an iodine atom. Of these, a chlorine atom and afluorine atom are preferable as Y¹, and a chlorine atom is morepreferable.

In general formula (I), n represents either 0 or 1. When n is 1, thebonding position of Y¹ is not particularly limited, but a bondingposition that forms a 4-substituted benzyl group is preferred.

In general formula (I), A represents a nitrogen atom or a methine group.Among these, a nitrogen atom is preferable as A.

A preferred specific example of the azole derivative (I) is an azolederivative represented by general formula (Ia) below.

In this instance, in general formula (Ia), Y² represents a chlorineatom, a fluorine atom, or a hydrogen atom.

Additionally, in the azole derivative (I), there are stereoisomers basedon the steric configuration of the organic groups that are bonded to thecyclopentane ring, and there are optical isomers of each stereoisomer.Accordingly, the azole derivative (I) may be either a substance thatincludes these isomers independently, or a substance that includes anarbitrary ratio of each isomer. Of these, an azole derivative in whichthe hydroxy group bound to the cyclopentane ring and —R¹ are cis-typesubstances is preferable, and an azole derivative in which the hydroxygroup bound to the cyclopentane ring, —R¹, and a substituted orunsubstituted benzyl group are cis-type substances is more preferable.

In addition, the agricultural or horticultural chemical may include twoor more types of azole derivative (I) in which at least one of R¹, R²,A, Y¹, and n differs.

The azole derivative (I) exhibits excellent fungicidal activity againstmany types of fungi that cause plant diseases. Furthermore, the chemicalcontaining the azole derivative (I) as an active ingredient has lowtoxicity toward human and animals and excellent safety in handling, andcan exhibit a high controlling effect against a wide variety of plantdiseases.

The method of producing the azole derivative (I) is not particularlylimited, and the azole derivative (I) can be produced using a publiclyknown production method.

(1-2) Compound Having a Cell Membrane Ergosterol Biosynthesis InhibitoryCapacity

The agricultural or horticultural chemical of the present inventioncontains, as one of the active ingredients, a compound having a cellmembrane ergosterol biosynthesis inhibitory capacity (called an“ergosterol biosynthesis inhibiting compound” hereafter) in addition tothe azole derivative (I). The agricultural or horticultural chemicalcontaining an ergosterol biosynthesis inhibiting compound and the azolederivative (I) as active ingredients can reduce the amount of dispersionof the chemicals required to obtain the same degree of effect as in thecase in which an ergosterol biosynthesis inhibiting compound is usedalone as a single agent.

Examples of ergosterol biosynthesis inhibiting compounds includeazaconazole, bitertanol, bromoconazole, difenoconazole, cyproconazo le,diniconazole, fenarimol, fenbuconazole, fenpropidine, fenpropimorph,triazole, flutriafol, hexaconazole, imazalil, imibenconazole,metconazole, ipconazole, myclobutanil, nuarimol, pefurazoate,penconazole, procloraz, propiconazole, prothioconazole, epoxiconazole,simeconazole, spiroxamine, tebuconazole, tetraconazole, triadimefon,triadimenol, triflumizol, triforine, triticonazole, fenhexamid,dodemorph, aldimorph, piperalin, fenhexamid, fenpyrazamine, etaconazole,tridemorph, and the like. Of these, metconazole, prothioconazole,epoxiconazole, propiconazole, ipconazole, tebuconazole, fenpropimorph,and fenpropidine are preferable. An agricultural or horticulturalchemical containing at least any one of metconazole, prothioconazole,epoxiconazole, propiconazole, ipconazole, tebuconazole, fenpropimorph,and fenpropidine exhibits particularly high activity. One type ofergosterol biosynthesis inhibiting compound may be contained in theagricultural or horticultural chemical, or a plurality of types ofcompounds may be contained.

Metconazole, prothioconazole, epoxiconazole, propiconazole, ipconazole,tebuconazole, fenpropimorph, fenpropidine, and other ergosterolbiosynthesis inhibiting compounds can be obtained from commerciallyavailable formulations or produced using publicly known productionmethods.

(2) Formulation

In an embodiment of the agricultural or horticultural chemical of thepresent invention, the mixing ratio of the azole derivative (I) to theergosterol biosynthesis inhibiting compound (for cases in which aplurality of compounds are used, the total amount thereof) is, in termsof weight ratio, preferably from 1000:1 to 1:1000, more preferably from750:1 to 1:750, and even more preferably from 500:1 to 1:500. Note thatfor cases in which a plurality of active ingredients are used asergosterol biosynthesis inhibiting compounds, the mixing ratio of theplurality of ergosterol biosynthesis inhibiting compounds can be setappropriately depending on the application of the chemicals.

The agricultural or horticultural chemical may contain solid carriers,liquid carriers (diluents), surfactants, or other formulation aids, inaddition to the active ingredients described above. Thus, the form ofthe agricultural or horticultural chemical may take on various formssuch as a powder, a wettable powder, granules, or an emulsion.

In the agricultural or horticultural chemical, the total content of theazole derivative (I) and the ergosterol biosynthesis inhibiting compoundis preferably from 0.1 to 95 wt. %, more preferably from 0.5 to 90 wt.%, and even more preferably from 2 to 80 wt. % relative to the totalamount of the agricultural or horticultural chemical.

Examples of solid carriers that are used as formulation aids includetalc, kaolin, bentonite, diatomaceous earth, white carbon, clay, and thelike. Examples of liquid carriers that are used as formulation aidsinclude water, xylene, toluene, chlorobenzene, cyclohexane,cyclohexanone, dimethylsulfoxide, dimethylformamide, alcohol, and thelike. Surfactants that are used as formulation aids may be used fordifferent purposes depending on their effect. For example, in the caseof an emulsifier, polyoxyethylene alkyl aryl ether, polyoxyethylenesorbitan monolaurate, and the like may be used. In the case of adispersant, lignin sulfonate, dibutyl napthalene sulfonate, and the likemay be used. In the case of a wetting agent, alkyl sulfonate, alkylphenyl sulfonate, and the like may be used.

The agricultural or horticultural chemical may be used in an unmodifiedstate, or may be used after dilution to a predetermined concentrationusing a diluent such as water. When used after being diluted, the totalconcentration of the active ingredients is preferably within the rangeof from 0.001 to 1.0% relative to the total amount of the chemical agentafter dilution.

Since the agricultural or horticultural chemical of the presentinvention exhibits a synergistic effect in its controlling effectagainst plant diseases, the agricultural or horticultural chemical canreduce the used amount of the compounds required to obtain the samedegree of effect as in cases in which the azole derivative (I) or theergosterol biosynthesis inhibiting compound is used alone as a singleagent. For this reason, toxicity in non-target organisms andenvironmental load can be reduced. In addition, it is anticipated thatthe emergence of chemical-resistant fungi can be suppressed because theused amount of the respective compounds can be reduced. Furthermore,since the agricultural or horticultural chemical of the presentinvention contains two ingredients having significantly differentmolecular structures as the active ingredients for the plant diseasecontrolling effect, the agricultural or horticultural chemical offers abroad spectrum of disease control.

The agricultural or horticultural chemical may be prepared byformulating each of the active ingredients separately and then mixingthem to produce a formulated agricultural or horticultural chemical.Therefore, a product for controlling plant diseases separatelycontaining the azole derivative (I) and an ergosterol biosynthesisinhibiting compound as combination preparations by which ingredients aremixed for use in controlling plant diseases, is also included in thescope of the present invention. When two or more ergosterol biosynthesisinhibiting compounds are contained, the two or more ergosterolbiosynthesis inhibiting compounds may also be separate from one another.

(3) Plant Disease Controlling Effect

The agricultural or horticultural chemical of the present inventionexhibits a controlling effect against a wide range of plant diseases.Examples of applicable diseases include the following. Note that, in theparenthesis after each disease name, major pathogenic fungus(fungi) thatcauses the disease is(are) indicated.

That is, applicable diseases include soybean rust (Phakopsorapachyrhizi, Phakopsora meibomiae), soybean septoria brown spot (Septoriaglycines), soybean purpura (Cercospora kikuchii), rice blast(Pyricularia grisea), rice sesame leaf blight (Cochliobolus miyabeanus),rice bacterial leaf blight (Xanthomonas oryzae), rice sheath blight(Rhizoctonia solani), rice stem rot (Helminthosporium sigmoideun), ricebakanae disease (Gibberella fujikuroi), rice seedling blight (Pythiumaphanidermatum), barley powdery mildew (Erysiphe graminis f. Sp hordei),barley stem rust (Puccinia graminis), barley yellow rust (Pucciniastriiformis), barley mottle-leaf (Pyrenophora graminea), barley scald(Rhynchosporium secalis), barley loose kernel smut (Ustilago nuda),barley net blotch (Pyrenophora teres), barley Fusarium head blight(Fusarium graminearum, Microdochium nivale ), wheat powdery mildew(Erysiphe graminis f. Sp tritici), wheat leaf rust (Puccinia recondita),wheat yellow rust (Puccinia striiformis), wheat eyespot disease(Pseudocercosporella herpotrichoides), wheat Fusarium head blight(Fusarium graminearum, Microdochium nivale ), wheat glume blotch(Phaeosphaeria nodorum), wheat leaf blight (Septoria tritici), wheatpink snow mold (Microdochium nivale ), wheat damping off (Gaeumannomycesgraminis), wheat black spot disease (Epicoccum spp), wheat maculardisease (Pyrenophora tritici-repentis), corn smut (Ustilago maydis),corn anthracnose (Colletotrichum graminicola), corn brown spot disease(Kabatiella zeae), corn gray leaf spot (Cercospora zeae-maydis),northern leaf blight (Setosphaeria turcica), corn northern leaf spot(Cochliobolus carbonum), corn leaf spot (Physoderma maydis), corn rust(Puccinia spp), corn sesame leaf blight (Bipolaris maydis), corn yellowsesame leaf blight (Phyllosticta maydis), corn Fusarium head blight(Gibberella zeae), sugarcane rust (Puccinia spp), Cucurbitaceae powderymildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum lagenarium,Glomerella cingulata), cucumber downy mildew (Pseudoperonosporacubensis), cucumber gray plague (Phytophthora capsici), cucumber vinewilt (Fusarium oxysporum f.sp.cucumerinum), watermelon vine wilt(Fusarium oxysporum f.sp. niveum), apple powdery mildew (Podosphaeraleucotricha), apple scab (Venturia inaequalis), apple monilia disease(Monilinia mali), apple leaf spot disease (Alternaria alternata), applefranc disease (Valsa mali), pear black spot disease (Alternariakikuchiana), pear powdery mildew (Phyllactinia pyri), pear chocolatespot (Gymnosporangium asiaticum), pear scab (Venturia nashicola),strawberry powdery mildew (Sphaerotheca humuli), stone fruit orchardbrown rot (Monilinia fructicola), citrus blue mold (Penicilliumitalicum), grape powdery mildew (Uncinula necator), grape downy mildew(Plasmopara viticola), grape evening rot (Glomerella cingulata), graperust (Phakopsora ampelopsidis), tomato powdery mildew (Erysiphecichoracearum), tomato early blight (Alternaria solani), eggplantpowdery mildew (Erysiphe cichoracearum), potato early blight (Alternariasolani), tobacco powdery mildew (Erysiphe cichoracearum), tobaccochocolate spot (Alternaria longipes), sugar beet brown spot Cercosporabeticola (Cercospora beticola), radish chlorosis (Fusarium oxysporumf.sp.raphani), gray mold disease that affects a variety of crops(Botrytis cinerea) and rot (Sclerotinia sclerotiorum), and the like.

In addition, examples of applicable plants include wild plants,cultivars, plants and cultivars bred by conventional hybridizing orplasmogamy, and genetically recombinant plants and cultivars obtained bygene manipulation. Examples of genetically recombined plants andcultivars include herbicide-tolerant crops, pest-resistant crops inwhich an insecticidal protein-producing gene has been recombined,pathogen-resistant crops in which a pathogen resistancederivative-producing gene has been recombined, taste-improved crops,yield-improved crops, preservation-improved crops, yield-improved crops,and the like. Specific examples of genetically recombined cultivarsinclude the brand names Roundup Ready, Liberty Link, Clearfield,Yieldgard, Herculex, Bollgard, and the like.

In addition, an embodiment of the agricultural or horticultural chemicalof the present invention exhibits an effect of increasing the amount ofharvest by regulating the growth or an effect of enhancing the qualityof a wide variety of crops and garden plants. Examples of these cropsinclude wheats such as wheat, barley, and oat, food crops such as rice,rapeseed, sugar cane, corn, maize, soy bean, pea, peanut, and sugarbeet, cabbage, garlic, radish, carrot, apple, pear, citruses such asmandarin orange, orange and lemon, peach, cherry, avocado, mango,papaya, red pepper, cucumber, melon, strawberry, tobacco, tomato,eggplant, lawn, chrysanthemum, azalea, and other decorative plants.

Furthermore, the azole derivative (I) exhibits an excellent effect inprotecting materials from a wide variety of harmful microorganisms thaterode industrial materials, and can be used as an active ingredient forindustrial material protectants. Because of this, an embodiment of theagricultural or horticultural chemical of the present invention can bealso used as an industrial material protectant.

(4) Other Active Ingredients

The agricultural or horticultural chemical of the present invention canbe used in combination with other known active ingredients (activeingredients contained in fungicides, insecticides, miticides, orherbicides, and plant growth regulating agents) in addition to theactive ingredients described above in order to enhance the performanceas an agricultural or horticultural chemical.

Plant Disease Controlling Method

The agricultural or horticultural chemical of the present invention canbe used not only in foliage treatment such as foliage spraying but alsoin non-foliage treatment such as seed treatment, soil-drenchingtreatment, or water surface treatment. Therefore, the method ofcontrolling plant diseases of the present invention comprises a step ofperforming foliage treatment or non-foliage treatment using theagricultural or horticultural chemical described above. When non-foliagetreatment is performed, the amount of labor required can be reduced incomparison to when foliage treatment is performed.

In the case of application by seed treatment, the chemical is depositedon seeds by mixing and stirring a wettable powder and a powder and thelike with seeds or immersing seeds in a diluted wettable powder or thelike. The total amount of active ingredients used in the case of seedtreatment is, for example, from 0.01 to 10,000 g and preferably from 0.1to 1,000 g per 100 kg of seeds. Seeds that have been treated with theagricultural or horticultural chemical may be used in the same manner asordinary seeds.

In the case of application by irrigation treatment, a planting hole orthe vicinity thereof may be treated with granules or the like at thetime of the transplantation of seedling or the like, or seeds or theearth around a plant may be treated with granules, a wettable powder, orthe like. The total amount of active ingredients used in the case ofirrigation treatment is, for example, from 0.01 to 10,000 g andpreferably from 0.1 to 1000 g per 1 m² of agricultural or horticulturalarea.

In the case of application by water surface treatment, the water surfaceof a paddy field may be treated with granules or the like. The totalamount of active ingredients used in the case of water surface treatmentis, for example, from 0.1 to 10,000 g and preferably from 1 to 1,000 gper 10 a of the paddy field.

The total amount of active ingredients used for foliar spraying is, forexample, from 20 to 5,000 g and preferably from 50 to 2,000 g per 1 haof the agricultural or horticultural area such as a field, a rice paddy,an orchard, or a greenhouse.

Additionally, since the concentration and quantity used differ dependingon the form of the agent, time of use, usage method, usage location,target crops and the like, they may be increased or decreased within theabove ranges.

SUMMARY

As described above, the agricultural or horticultural chemical of thepresent invention has a constitution containing a plurality of activeingredients, the agricultural or horticultural chemical comprising: asone of the active ingredients, an azole derivative represented bygeneral formula (I) below; and, as another one of the activeingredients, a compound having a cell membrane ergosterol biosynthesisinhibitory capacity.

In formula (I), R¹ represents an alkyl group having from 1 to 6 carbons;R² represents a hydrogen atom, an alkyl group having from 1 to 3carbons, an alkenyl group having from 2 to 3 carbons, or an alkynylgroup having from 2 to 3 carbons; A represents a nitrogen atom or amethine group; Y¹ represents a halogen atom; and n represents either 0or 1.

In the agricultural or horticultural chemical of the present invention,the compound having a cell membrane ergosterol biosynthesis inhibitorycapacity is preferably at least any one of metconazole, prothioconazole,epoxiconazole, propiconazole, ipconazole, tebuconazole, fenpropimorph,and fenpropidine.

Furthermore, the agricultural or horticultural chemical of the presentinvention is preferably used as a fungicide.

In addition, in the agricultural or horticultural chemical according tothe present invention, it is preferable that the above-mentioned azolederivative be an azole derivative represented by general formula (Ia)below.

Additionally, in general formula (Ia), Y² represents a chlorine atom, afluorine atom or a hydrogen atom.

The product for controlling plant diseases of the present invention hasa constitution separately comprising, as a combination preparation bywhich a plurality of active ingredients are mixed for use: an azolederivative represented by general formula (I) above; and a compoundhaving a cell membrane ergosterol biosynthesis inhibitory capacity.

The method of controlling plant diseases of the present inventioncomprises a step of performing foliage treatment or non-foliagetreatment using the agricultural or horticultural chemical describedabove.

Embodiments of the present invention will be described in furtherdetails hereinafter using working examples. Of course, the presentinvention is not limited to the examples below, and it goes withoutsaying that various modes are possible with regard to the detailsthereof. Furthermore, the present invention is not limited to theembodiments described above, and various modifications are possiblewithin the scope indicated in the claims. Embodiments obtained byappropriately combining the technical means disclosed by the embodimentsare also included in the technical scope of the present invention. Inaddition, all of the documents disclosed in the present specificationare hereby incorporated by reference.

EXAMPLES

The antimicrobial action of a mixed formulation of methyl3-(4-chlorobenzyl)-2-hydroxy-1-methyl-2-(1H-1,2,4-triazole-1-ylmethyl)cyclopentanecarbonate (compound (1) hereafter) and a compound having an ergosterolbiosynthesis inhibitory capacity was tested.

Test Example 1 In Vitro Antimicrobial Activity Test Using Compound (1)and Prothioconazole

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and prothioconazole against Septoria tritici was tested.

A plate culture medium containing chemicals was prepared by mixingcompound (1) alone, prothioconazole alone, or compound (1) andprothioconazole in a PDA culture medium at a prescribed concentration.Meanwhile, Septoria tritici was punched out from the vicinity of aSeptoria tritici colony that was cultured in advance on another plateculture medium free of the chemicals using a cork borer having adiameter of 4 mm, and inoculated on the PDA plate culture medium inwhich the chemicals were mixed. After culturing at 25° C. for 14 days,the diameter of the grown colony was measured. The fungal growthinhibition rate was determined by comparing this diameter of the growncolony and the diameter of the colony on the culture medium free of thechemicals, and by using the following formula R=100(dc−dt)/dc.Additionally, in the above formula, R represents a fungal growthinhibition rate (%), dc represents the diameter of a colony on anuntreated plate, and dt represents the diameter of a colony on achemical-treated plate. Next, the synergistic effect of the two types ofchemicals was determined with a method using the Colby's formula(below):

Inhibition rate when used as a mixture (theoretical value)=α+((100−α)×β)/100 Note that, in the formula above, α and β respectivelyrepresent the inhibition rates of the compounds during single use of thecompounds.

The results are shown in Table 1. The growth inhibition rate upon mixingthe compound (1) and prothioconazole was greater than the theoreticalvalue calculated from the inhibition rates upon using each of thecompounds alone, and it is clear that the compound (1) andprothioconazole exhibited a synergistic effect.

TABLE 1 Fungal growth inhibition rate (%) Compound (1) ProthioconazoleMeasured Theoretical ppm ppm value value 0 2.5 100 — 0 0.625 51 — 00.156 21 — 0 0.039 10 — 0 0.010 0 — 0.005 0 35 — 0.005 2.5 100 100 0.0050.625 84 68 0.005 0.156 63 49 0.005 0.039 51 42 0.005 0.010 37 35

Test Example 2 In Vitro Antimicrobial Activity Test Using Compound (1)and Metconazole

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and metconazole against Septoria tritici was tested.

Tests and assessments were performed in the same manner as in TestExample 1 with the exception that metconazole was used in place ofprothioconazole.

The results are shown in Table 2. The growth inhibition rate upon mixingthe compound (1) and metconazole was greater than the theoretical valuecalculated from the inhibition rates upon using each of the compoundsalone, and it is clear that the compound (1) and metconazole exhibited asynergistic effect.

TABLE 2 Fungal growth inhibition rate (%) Compound (1) MetconazoleMeasured Theoretical ppm ppm value value 0 2.5 98 — 0 0.625 56 — 0 0.15611 — 0 0.039 0 — 0 0.010 0 — 0.02 0 3 — 0.02 2.5 99 98 0.02 0.625 58 570.02 0.156 30 14 0.02 0.039 11 3 0.02 0.010 14 3

Test Example 3 In Vitro Antimicrobial Activity Test Using Compound (1)and Epoxiconazole

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and epoxiconazole against Fusarium graminearum was tested.

A plate culture medium containing chemicals was prepared by mixingcompound (1) alone, epoxiconazole alone, or compound (1) andepoxiconazole in a PDA culture medium at a prescribed concentration.Fusarium graminearum was punched out from the vicinity of a Fusariumgraminearum colony using a cork borer having a diameter of 4 mm, andinoculated on the PDA plate culture medium in which the chemicals weremixed. After culturing at 25° C. for 3 days, the diameter of the growncolony was measured. The fungal growth inhibition rate was determined inthe same manner as in Test Example 1 by comparing this diameter of thegrown colony and the diameter of the colony on the culture medium freeof the chemicals. In addition, the synergistic effect was determinedusing a method that used Colby's formula in the same manner as TestExample 1.

The results are shown in Table 3. The growth inhibition rate upon mixingthe compound (I) and epoxiconazole was greater than the theoreticalvalue calculated from the inhibition rates upon using each of thecompounds alone, and it is clear that the compound (1) and epoxiconazoleexhibited a synergistic effect.

TABLE 3 Fungal growth inhibition rate (%) Compound (1) EpoxiconazoleMeasured Theoretical ppm ppm value value 0 2.50 88 — 0 0.63 57 — 0 0.1639 — 0 0.04 27 — 0 0.01 22 — 1.25 0 93 — 1.25 2.50 100 99 1.25 0.63 10097 1.25 0.16 98 96 1.25 0.04 98 95 1.25 0.01 98 95

Test Example 4 In Vitro Antimicrobial Activity Test Using Compound (1)and Propiconazole

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and propiconazole against Microdochium nivale was tested.

A plate culture medium containing chemicals was prepared by mixingcompound (1) alone, propiconazole alone, or compound (1) andpropiconazole in a PDA culture medium at a prescribed concentration.Microdochium nivale was punched out from the vicinity of a Microdochiumnivale colony that was cultured in advance on another plate culturemedium free of the chemicals using a cork borer having a diameter of 4mm, and inoculated on the PDA plate culture medium in which thechemicals were mixed. After culturing at 25° C. for 3 days, the diameterof the grown colony was measured. The fungal growth inhibition rate wasdetermined in the same manner as in Test Example 1 by comparing thisdiameter of the grown colony and the diameter of the colony on theculture medium free of the chemicals. In addition, the synergisticeffect was determined using a method that used Colby's formula in thesame manner as Test Example 1.

The results are shown in Table 4. The growth inhibition rate upon mixingthe compound (1) and propiconazole was greater than the theoreticalvalue calculated from the inhibition rates upon using each of thecompounds alone, and it is clear that the compound (1) and propiconazoleexhibited a synergistic effect.

TABLE 4 Fungal growth inhibition rate (%) Compound (1) PropiconazoleMeasured Theoretical ppm ppm value value 0 2.5 76 — 0 0.625 45 — 0 0.1560 — 0.313 0 26 — 0.313 2.5 95 83 0.313 0.625 64 59 0.313 0.156 39 26

Test Example 5 In Vitro Antimicrobial Activity Test Using Compound (1)and Tebuconazole

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and tebuconazole against Penicilium italicum was tested.

A plate culture medium containing chemicals was prepared by mixingcompound (1) alone, tebuconazole alone, or compound (1) and tebuconazolein a PDA culture medium at a prescribed concentration. Peniciliumitalicum was punched out from the vicinity of a Penicilium italicumcolony that was cultured in advance on another plate culture medium freeof the chemicals using a cork borer having a diameter of 4 mm, andinoculated on the PDA plate culture medium in which the chemicals weremixed. After culturing at 25° C. for 3 days, the diameter of the growncolony was measured. The fungal growth inhibition rate was determined inthe same manner as in Test Example 1 by comparing this diameter of thegrown colony and the diameter of the colony on the culture medium freeof the chemicals. In addition, the synergistic effect was determinedusing a method that used Colby's formula in the same manner as TestExample 1.

The results are shown in Table 5. The growth inhibition rate upon mixingthe compound (1) and tebuconazole was greater than the theoretical valuecalculated from the inhibition rates upon using each of the compoundsalone, and it is clear that the compound (1) and tebuconazole exhibiteda synergistic effect.

TABLE 5 Fungal growth inhibition rate (%) Compound (1) TebuconazoleMeasured Theoretical ppm ppm value value 0 10.00 100 — 0 2.50 87 — 00.63 68 — 0 0.16 30 — 0 0.04 3 — 1.25 0 83 — 1.25 10.00 100 100 1.252.50 100 98 1.25 0.63 100 94 1.25 0.16 98 88 1.25 0.04 98 83

Test Example 6 In Vitro Antimicrobial Activity Test Using Compound (1)and Ipconazole

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and ipconazole against Phaeosphaeria nodorum was tested.

A plate culture medium containing chemicals was prepared by mixingcompound (1) alone, ipconazole alone, or compound (1) and ipconazole ina PDA culture medium at a prescribed concentration. Phaeosphaerianodorum was punched out from the vicinity of a Phaeosphaeria nodorumcolony that was cultured in advance on another plate culture medium freeof the chemicals using a cork borer having a diameter of 4 mm, andinoculated on the PDA plate culture medium in which the chemicals weremixed. After culturing at 25° C. for seven days, the diameter of thegrown colony was measured. The fungal growth inhibition rate wasdetermined in the same manner as in Test Example 1 by comparing thisdiameter of the grown colony and the diameter of the colony on theculture medium free of the chemicals. In addition, the synergisticeffect was determined using a method that used Colby's formula in thesame manner as Test Example 1.

The results are shown in Table 6. The growth inhibition rate upon mixingthe compound (1) and ipconazole was greater than the theoretical valuecalculated from the inhibition rates upon using each of the compoundsalone, and it is clear that the compound (1) and ipconazole exhibited asynergistic effect.

TABLE 6 Fungal growth inhibition rate (%) Compound (1) IpconazoleMeasured Theoretical ppm ppm value value 0 0.63 76 — 0 0.16 62 — 0 0.0431 — 0 0.01 20 — 1.25 0 89 — 1.25 0.63 100 97 1.25 0.16 100 96 1.25 0.04100 92 1.25 0.01 100 91

Test Example 7 In Vitro Antimicrobial Activity Test Using Compound (1)and Fenpropimorph

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and fenpropimorph against Septoria tritici was tested.

A plate culture medium containing chemicals was prepared by mixingcompound (1) alone, fenpropimorph alone, or compound (1) andfenpropimorph in a PDA culture medium at a prescribed concentration.Meanwhile, Septoria tritici was punched out from the vicinity of aSeptoria tritici colony that was cultured in advance on another plateculture medium free of the chemicals using a cork borer having adiameter of 4 mm, and inoculated on the PDA plate culture medium inwhich the chemicals were mixed. After culturing at 25° C. for 14 days,the diameter of the grown colonies were measured, and the fungal growthinhibition rate was determined by comparing the diameter with thediameter of a colony on the culture medium that did not include thechemicals in the same manner as Test Example 1. In addition, thesynergistic effect was determined using a method that used Colby'sformula in the same manner as Test Example 1.

The results are shown in Table 7. The growth inhibition rate upon mixingthe compound (1) and fenpropimorph was greater than the theoreticalvalue calculated from the inhibition rates upon using each of thecompounds alone, and it is clear that the compound (1) and fenpropimorphexhibited a synergistic effect.

TABLE 7 Fungal growth inhibition rate (%) Compound (1) FenpropimorphMeasured Theoretical ppm ppm value value 0 10.00 45 — 0 2.50 42 — 0 0.6323 — 0 0.16 21 — 0 0.04 16 — 1.25 0 70 — 1.25 10.00 91 84 1.25 2.50 9183 1.25 0.63 91 77 1.25 0.16 83 77 1.25 0.04 80 75

Test Example 8 In Vitro Antimicrobial Activity Test Using Compound (1)and Fenpropidine

In this test example, the antimicrobial action of a mixed formulation ofcompound (1) and fenpropidine against Septoria tritici was tested.

Tests and assessments were performed in the same manner as in TestExample 7 with the exception that fenpropidine was used in place offenpropimorph.

The results are shown in Table 8. The growth inhibition rate upon mixingthe compound (1) and fenpropidine was greater than the theoretical valuecalculated from the inhibition rates upon using each of the compoundsalone, and it is clear that the compound (1) and fenpropidine exhibiteda synergistic effect.

TABLE 8 Fungal growth inhibition rate (%) Compound (1) FenpropidineMeasured Theoretical ppm ppm value value 0 10.00 40 — 0 2.50 38 — 0 0.6340 — 0 0.16 0 — 0 0.04 0 — 1.25 0 77 — 1.25 10.00 100 86 1.25 2.50 90 861.25 0.63 93 86 1.25 0.16 88 77 1.25 0.04 82 77

INDUSTRIAL APPLICABILITY

The present invention can be suitably used as an active ingredient ofcontrolling agents that can control plant diseases while minimizingharmful effects to the plants.

1. An agricultural or horticultural chemical containing a plurality of active ingredients, the agricultural or horticultural chemical comprising: as one of active ingredients, an azole derivative represented by general formula (I); and, as another one of the active ingredients, a compound having a cell membrane ergosterol biosynthesis inhibitory capacity:

wherein, R¹ represents an alkyl group having from 1 to 6 carbons, R² represents a hydrogen atom, an alkyl group having from 1 to 3 carbons, an alkenyl group having from 2 to 3 carbons or an alkynyl group having from 2 to 3 carbons, A represents a nitrogen atom or a methine group, Y¹ represents a halogen atom, and n represents either 0 or
 1. 2. The agricultural or horticultural chemical according to claim 1, wherein the compound having a cell membrane ergosterol biosynthesis inhibitory capacity is at least any one of metconazole, prothioconazole, epoxyconazole, propiconazole, ipconazole, tebuconazole, fenpropimorph, and fenpropidine.
 3. The agricultural or horticultural chemical according to claim 1, wherein the agricultural or horticultural chemical is used as a fungicide.
 4. The agricultural or horticultural chemical according to claim 1, wherein the azole derivative is an azole derivative represented by general formula (Ia):

wherein, Y² is a chlorine atom, a fluorine atom or a hydrogen atom.
 5. A product for controlling plant diseases separately comprising, as a combination preparation by which a plurality of active ingredients are mixed for use: an azole derivative represented by general formula (I); and a compound having a cell membrane ergosterol biosynthesis inhibitory capacity:

wherein, R¹ represents an alkyl group having from 1 to 6 carbons, R2 represents a hydrogen atom, an alkyl group having from 1 to 3 carbons, an alkenyl group having from 2 to 3 carbons or an alkynyl group having from 2 to 3 carbons, A represents a nitrogen atom or a methine group, Y¹ represents a halogen atom, and n represents either 0 or
 1. 6. A method of controlling plant diseases comprising a step of performing foliage treatment or non-foliage treatment using the agricultural or horticultural chemical described in any one of claims 1 to
 4. 